Day told the story of graduating from Merrimack with two options: move to New York City to pursue acting, or take an entry-level position at Fidelity Investments that he had accidentally landed by treating the interview like an audition. The job was real money — more than anyone had ever offered him. He was tempted to use it as a safe stepping stone. But he turned it down, moved to the city, bussed tables, and lived in a cockroach-infested basement apartment next to a garbage chute. He couldn't have made a better decision, because if he was going to fail, he wanted to fail doing what he loved.